I stopped using wired headphones before I had a device without a headphone jack.

I found the cord infuriating, always seemed to get caught or tangled on things, always making sensitive skin contact (like just beneath my jawline) where I was forever readjusting it and sometimes the cords lifted the headphone out of my ear.

Conversely, I’ve had three pairs of wireless headphones. First pair didn’t like getting christened in the washing machine, second pair is still going strong and third pair are AirPod Pros I bought before a flight for the noise cancellation which are also going strong. Maybe I’ve outsmarted the whole of Apple’s engineering/marketing department but I’ve never felt like the sets I’ve had are underperforming on battery life and have no reason to buy sets to replace the working ones I have. The small conveniences, like not being tethered to my phone and freedom from cords, have absolutely made the change to wireless worth it to me.

The biggest and most obvious downside against wireless headphones is compatibility and price.